Fused ring pyrazolone derivative and preparation method thereof

A kind of technology of cyclopyrazolone and cyclopyrazolone, which is applied in the field of cyclopyrazolone derivative and preparation thereof, and can solve the limitation of synthesis and development of cyclopyrazolone, large demand of catalyst and raw material. Restricted sources and other issues, to achieve the effects of excellent pharmacological activity, high stability, and simple and easy-to-obtain reaction raw materials

Pending Publication Date: 2020-06-12
ANHUI NORMAL UNIV
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  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

The limitation of this type of reaction can only be realized under metal catalysis; (3) multi-component reaction: multi-component reaction is one of the methods for efficiently constructing chemical bonds, but it often has the following disadvantages, 1) the uncertainty of the reaction 2) more by-products; 3) a large amount of catalyst required
[0004] The above defects in the synthetic method of cyclic pyrazolones mainly contain the following: (1) the source of raw materials is limited, as in the above method (1), only substrates with unsaturated structures can be used, but saturated The alkane substrates limit the synthetic development of specific structure and ring pyrazolones; as method (2) can only be applicable to metal carbene substrates; (2) usually use CO gas or metal to realize carbonylation reaction Carbonyl complex realizes the introduction of carbonyl structure in the substrate

Method used

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  • Fused ring pyrazolone derivative and preparation method thereof
  • Fused ring pyrazolone derivative and preparation method thereof
  • Fused ring pyrazolone derivative and preparation method thereof

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preparation example Construction

[0032] The invention provides a kind of preparation method of cyclic pyrazolone derivative, and described preparation method comprises:

[0033] (1) [Cp*IrCl 2 ] 2 , AgOAc, pyrazolone compound, azide compound and solvent mixed reaction;

[0034] (2) The cyclic pyrazolone derivatives were obtained by following the reaction by TLC and separating by column chromatography.

[0035] In a preferred embodiment of the present invention, the pyrazolone compound is selected from N-phenyl-2-trifluoromethyl-pyrazolone, N-(3-methylphenyl)-2- Trifluoromethyl-pyrazolone, N-(3,5-dimethylphenyl)-2-trifluoromethyl-pyrazolone, N-(4-methylphenyl)-2-tri Fluoromethyl-pyrazolone, N-(4-ethylphenyl)-2-trifluoromethyl-pyrazolone, N-(4-methoxyphenyl)-2-trifluoromethyl -pyrazolone, N-(4-isopropylphenyl)-2-trifluoromethyl-pyrazolone or N-(4-tert-butylphenyl)-2-trifluoromethyl-pyridine One of the oxazolinones.

[0036] In a preferred embodiment of the present invention, the azide compound is selected...

Embodiment 1

[0048] Add [Cp*IrCl 2 ] 2 (0.01 mmol), AgOAc (0.05 mmol), N-phenyl-2-trifluoromethyl-pyrazolone (0.25 mmol), benzoyl azide (0.5 mmol), 1,2-dichloroethane (3mL), reacted at 70°C for 8h, followed the reaction by TLC, after the reaction, extracted, dried, and separated by column chromatography (developing agent petroleum ether / ethyl acetate v / v=8:1), that is, the yield of 76% Obtained pure white solid compound A1;

[0049]

[0050] The H NMR and C NMR data of compound A1 are as follows:

[0051] 1 H NMR (500MHz, CDCl 3 )δ8.26(d, J=8.0Hz, 1H), 8.12(d, J=8.5Hz, 1H), 7.93(t, J=7.5Hz, 1H), 6.29(s, 1H);

[0052] 13 C NMR (125MHz, CDCl 3 )δ156.2, 148.4, 144.8 (q, J C-F =39.1Hz), 138.0, 137.6, 131.5, 127.9, 120.8 (q, J C-F =268.0Hz), 115.4, 111.5, 88.6;

[0053] It can be seen that the single peak at 6.29 ppm and the double peak at 8.26 ppm in the proton NMR spectrum can confirm the formation of the target product.

Embodiment 2

[0055] Add [Cp*IrCl 2 ] 2 (0.01mmol), AgOAc (0.05mmol), N-(3-methylphenyl)-2-trifluoromethyl-pyrazolone (0.25mmol), benzoyl azide (0.5mmol), 1, 2-Dichloroethane (3mL), reacted at 70°C for 8h, followed the reaction by TLC, after the reaction, extracted, dried, and separated by column chromatography (developer petroleum ether / ethyl acetate v / v=8:1), that is A pure white solid compound A2 can be obtained in a yield of 71%;

[0056]

[0057] The H NMR and C NMR data of compound A2 are as follows:

[0058] 1 H NMR (500MHz, CDCl 3 )δ8.12(d, J=8.5Hz, 1H), 7.93(s, 1H), 7.34(d, J=8.0Hz, 1H), 6.27(s, 1H), 2.57(s, 3H);

[0059] 13 C NMR (125MHz, CDCl 3 )δ156.3, 150.3, 148.5, 144.6 (q, J C-F =39.1Hz), 137.5, 131.4, 129.1, 120.9 (q, J C-F =267.8Hz), 115.4, 108.9, 88.5, 22.8;

[0060] It can be seen that the single peak at 6.27ppm and the double peak at 8.12ppm in the proton NMR spectrum can confirm the formation of the target product.

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Abstract

The invention relates to the field of organic synthesis, and discloses a fused ring pyrazolone derivative and a preparation method thereof. The preparation method comprises the steps: (1) mixing [Cp *IrCl2] 2, AgOAc, pyrazolone compounds, azide compounds and a solvent for a reaction; and (2) carrying out TLC tracking reaction and column chromatography separation to obtain the fused ring pyrazolone derivative. The preparation method has the advantages of easily available raw materials, high stability, high yield, simple reaction conditions and the like.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a cyclic pyrazolone derivative and a preparation method thereof. Background technique [0002] Pyrazolone compounds are a common class of useful nitrogen- and oxygen-containing heterocyclic compounds, which are widely used in organic synthesis, material science, and medicine. In the field of organic synthesis, pyrazolone has multiple reaction centers, which can realize a variety of chemical transformations; in material science, pyrazolone can have a larger conjugated structure, and has important applications in organic light-emitting materials In the field of medicine, various drugs containing pyrazolone are common: phenylbutazone, hydroxybutazone, indomethacin, sulindac, mefenamic acid, clofenamic acid, diclofenac, ibuprofen Fen and other antipyretic and analgesic drugs, among which pyrazolone drugs are the most famous antipyretic and analgesic drugs such as Analgin. [0003] ...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 左有鹏何心伟周俏华
Owner ANHUI NORMAL UNIV
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